Dear Anna,

I’m a 38-year-old woman and recently reconnected with my ex-boyfriend from college, who’s now 40. We dated for two years when we were 22 and 24, and it was intense and meaningful before life pulled us in different directions.

We’ve been back together for about five months now, and he’s everything I remembered, except for one massive problem: his ex-wife. They were married for eight years and have been divorced for just over a year. They don’t have kids or pets. Despite this, they’re still completely entangled. They pay for a shared storage unit with furniture and belongings that he has not gone through once since he moved out. They’re still on each other’s car insurance and split a cellphone bill. He still has her as an emergency contact at work. Last month, she called him at 11 p.m. because her water heater broke, and he drove over to help her deal with it. He’s also lent her money twice since we’ve been dating — once to cover her rent when she was short. Meanwhile, when we go out, he insists on splitting everything because he’s “trying to be financially responsible after the divorce.”

I want to be understanding because divorce is messy and takes time to untangle, but I’m starting to feel like I’m dating someone who’s still married in every way except legally. When I bring it up, he says that he’s just being a decent person to someone he spent almost a decade with. Am I overreacting, or is this a sign he’s not actually ready to move on? — Second Place to the Ex-Wife

Dear SPEW,

You’re definitely in an odd kind of relationship limbo. You’re dating a man who’s technically single but functionally still in a relationship with his ex-wife — without the sex but with ottomans and AT&T bills.

Divorce is long and messy, yes, and I’m glad at least that they have an amicable relationship, but how long does it take to get your own phone plan? Like 30 minutes? The car insurance might be trickier if they co-own a vehicle, but late-night emergency calls? Financial bailouts? Those aren’t the hallmarks of ex decency — they’re codependency red flags — and your boyfriend is veering hard in that direction.

Taking care of his ex this way is a dynamic he needs to break if he wants your relationship to flourish — and that’s not just for your benefit, but for his and his ex-wife’s too. She needs to learn to handle her own emergencies and find other sources of support, and he needs to stop playing the hero, especially when it means deprioritizing you and the relationship he’s supposedly trying to build.

Here’s the thing about rekindled romances: They’re intoxicating because you get to skip past all the awkward early dating stuff and dive straight into the deep emotional connection you remember. But what you’re discovering is that the person you’re reconnecting with isn’t the 24-year-old you fell for — he’s a 40-year-old man who apparently hasn’t figured out how to close the door on his previous relationship.

That said, five months is still on the early side. You need to ask him (and yourself) some hard questions. Is this what being in a relationship with him actually looks like, or is this a temporary transition period while he figures his s—t out? Has he made any progress or changes in the time since you’ve been dating? If he’s shown zero interest or motivation in disentangling himself from her, then this isn’t a phase. This is the relationship.

Here’s what you need to do. Stop hinting and start being direct. Tell him, “I care about you, but I can’t build a future with someone who’s still operating like they’re married to their ex. I need to know what your actual plan is to separate your lives, and I need to see progress on that plan.” Then pay very close attention to whether he makes good on his promises — if he makes them.

If he doesn’t, then he’s choosing the path of least resistance with her over building something real with you.

If he actually hears you and starts making concrete changes — canceling the joint accounts, setting boundaries around her emergency calls, moving his stuff out of that storage unit — then maybe there’s hope. But words mean nothing here. You need to see action.

You deserve to be someone’s clear first choice, not their nostalgic backup plan while they keep one foot in their old marriage. Don’t settle for being the person he’s with while he’s still emotionally and financially tethered to someone else.

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